Search research articles

ABOUT JoVE

Overview Leadership Blog JoVE Help Center

AUTHORS

Publishing Process Editorial Board Scope & Policies Peer Review FAQ Submit

LIBRARIANS

Testimonials Subscriptions Access Resources Library Advisory Board FAQ

RESEARCH

JoVE Journal Methods Collections JoVE Encyclopedia of Experiments Archive

EDUCATION

JoVE Core JoVE Business JoVE Science Education JoVE Lab Manual Faculty Resource Center Faculty Site

Terms & Conditions of Use

Related Concept Videos

Regioselectivity and Stereochemistry of Hydroboration

Regioselectivity and Stereochemistry of Hydroboration

A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn...

Hydroboration-Oxidation of Alkenes

Hydroboration-Oxidation of Alkenes

In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.

Alkylation of β-Diester Enolates: Malonic Ester Synthesis

Alkylation of β-Diester Enolates: Malonic Ester Synthesis

Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.

Preparation of Alcohols via Addition Reactions

Preparation of Alcohols via Addition Reactions

Overview
The acid-catalyzed addition of water to the double bond of alkenes is a large-scale industrial method used to synthesize low-molecular-weight alcohols. An acidic atmosphere is required to allow the hydrogen in the water molecule to act as an electrophile and attack the double bond in an alkene. The addition of a proton to the double bond creates a carbocation intermediate. The proton preferentially bonds to the less substituted end of the double bond to create a more stable carbocation...

Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis

Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis

Acetoacetic ester synthesis is a method to obtain ketones from alkyl halides and β-keto esters. The reaction occurs in the presence of an alkoxide base that abstracts the acidic proton of the β-keto esters. The step results in an enolate ion which is doubly stabilized. The enolate then reacts with an alkyl halide via the SN2 process to produce an alkylated ester intermediate with a new C–C bond. The hydrolysis of the intermediate, followed by acidification, results in an...

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by

Same author

High-Precision Intrinsic Interactome Elucidation of Chimeric Antigen Receptors via Photocatalytic Micromapping (μMap-CAR).

Journal of the American Chemical Society·2026

Same author

Chemical biology tools for studying histone post-translational modifications.

Cell chemical biology·2026

Same author

Proximity labeling tools for studying chromatin interactomes.

Current opinion in chemical biology·2026

Same author

Design, Synthesis, and Application of Sulfonium Diazo Probes for Red-Light Photocatalytic Proximity Labeling.

ACS chemical biology·2026

Same author

RNase L regulates the antiviral proteome by accelerating mRNA decay, inhibiting nuclear mRNA export, and repressing transcription.

Cell reports·2026

Same author

A Polarity-Mismatched Photocatalytic Cross-Coupling Enables Diversity-Oriented Synthesis of aza-Heterocycles.

Organic letters·2026

Search research articles

Related Experiment Video

Updated: Apr 23, 2026

Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides

Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides

Published on: July 26, 2018

Chemoselective boronic ester synthesis by controlled speciation.

James W B Fyfe¹, Ciaran P Seath, Allan J B Watson

¹WestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow, G1 1XL (UK).

Angewandte Chemie (International Ed. in English)

|October 1, 2014

Summary

This summary is machine-generated.

Chemoselective synthesis of boronic esters is achieved by controlling boronic acid solution speciation. This strategy enables controlled homologation and iterative C-C bond formation for boronic esters.

Keywords:

boron chemoselectivity cross-coupling oligomerization palladium

More Related Videos

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Published on: November 9, 2019

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Published on: November 30, 2022

Related Experiment Videos

Last Updated: Apr 23, 2026

Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides

Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides

Published on: July 26, 2018

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Published on: November 9, 2019

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Published on: November 30, 2022

Area of Science:

Organic Chemistry
Catalysis
Synthetic Methodology

Background:

Boronic acids are versatile building blocks in organic synthesis.
Controlling the reactivity and speciation of boronic acids is crucial for selective transformations.
Existing methods for boronic ester synthesis often lack chemoselectivity.

Purpose of the Study:

To introduce a novel strategy for the chemoselective synthesis of boronic esters.
To demonstrate the utility of controlling boronic acid solution speciation.
To enable streamlined iterative catalytic C-C bond formation and controlled oligomerization.

Main Methods:

Manipulation of solution equilibria in a cross-coupling reaction milieu.
Utilizing palladium catalysis for C-C bond formation.
Employing aryl and alkenyl boronic acid pinacol esters as substrates.

Main Results:

Achieved chemoselective synthesis of boronic esters through speciation control.
Demonstrated formal homologation of aryl and alkenyl boronic acid pinacol esters.
Facilitated streamlined iterative catalytic C-C bond formation.
Provided a method for controlled oligomerization of sp(2)-hybridized boronic esters.

Conclusions:

Controlling boronic acid solution speciation is a powerful strategy for selective boronic ester synthesis.
This approach simplifies iterative C-C bond formation and enables controlled oligomerization.
The method offers a new pathway for constructing complex molecules from boronic esters.